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Some quick pointers:
1 Use lube. Use as much as needed (I strongly recommend astroglide)
2 Understand that her natural reaction will be to tense up and clench, and that this is counter intuitive to pleasurable anal sex. So have her practice breathing and getting in a very calm state of mind before you try to enter.
3 If she has trouble not tensing up remind her to focus on her breathing and reassure her.
4 Start slow, you cannot barrel in there. It will cause alot of pain and possible long-term damage. Start off with fingerplay if you can.
5) When it comes to entering with your penis; put your head against her ahole. Lightly press, do not be concerned with entering at this point.
6) Once your head is pressed against her butthole start to thrust and LIGHTLY pump (as if you were trying to dry hump her). Eventually she'll open up a little and you'll be in a little bit further. Now do not get excited, think that you're in so it's full speed ahead. You'll need to continue this process.
7) Once you've gotten a little bit inside of her keep slowly and lightly pumping, doing small and short strokes. Eventually she'll open up a bit more and you'll be a little deeper.
Repeat this process until you are all the way inside of her. Start slow and keep to short thrusts and SLOWLY work your way to a slightly faster pace and longer thrusts. Read her reactions to know how fast and how far you can go.
Hope that helps, feel free to pm me if have anymore questions.
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